4-Fluoroaniline → HCID 54527561, compound

HRID 375592Notes

Reaction equation

HRID 375592 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[NH:17][C:16]1[CH:18]=[CH:19][C:13]([F:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 54527561HCID 54527561, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-difluoronitrobenzene (5.5 ml), 4-fluoro aniline (14.2 ml) and sodium carbonate (5.3 g) was heated at 180° for 3 h. The reaction mixture was cooled to room temperature, then diluted with DCM, washed with water (50 ml), brine (2×50 ml) dried and evaporated under vacuum to give the crude compound (22.6 g), which was purified by flash chromatography with CH-EA 4/1 to give the title compound as an orange solid (12.35 g). M.p. 115°-6° T.l.c. CH-EA (10:1), Rf 0.52.

Workup

  1. temperaturewas heated at 180° for 3 h
  2. washwashed with water (50 ml), brine (2×50 ml)
  3. customdried
  4. customevaporated under vacuum
  5. customto give the crude compound (22.6 g), which
  6. customwas purified by flash chromatography with CH-EA 4/1

Sources & evidence

ORD record
ord-a3e2e78823584215a09a9c50abf199a1
Source dataset
uspto-grants-1996_01
Patent number
US05486514

Reaction notes

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